Influential Women in Captive Insurance: Sandy Bigglestone
Sandy Bigglestone, Deputy commissioner, Captive Insurance Division, Vermont Department of Financial Regulation
Sandy Bigglestone is responsible for the administration and regulation of captive insurance companies and risk retention groups in Vermont.
Having been with the Division since 1997, Bigglestone has a few decades of experience, and has had a successful career regulating captive insurance. She was appointed as Deputy Commissioner in 2022, after serving as a principal staff member to her predecessor for 14 years.
She is a Certified Public Accountant, Certified Financial Examiner, a Certified Public Manager with the State of Vermont, and earned an Associate Professional in Insurance Regulation designation from the National Association of Insurance Commissioners (NAIC).
In 2018, Bigglestone was a recipient of the Women to Watch Award presented by Business Insurance for her leadership, expertise, and accomplishments in the captive insurance industry.
How did you get started in the captive insurance industry?
Before joining the department, I was employed at a certified public accounting firm. My college degree was accounting, and I had my sights set on public accounting, not insurance, and certainly not insurance regulation. However, the firm had some audit clients that were captive insurance companies. I also audited public entity risk pools and governmental risk pools.
When an examiner position came up at the department, I was intrigued about the work and the greater good of the industry in terms of its impact on the Vermont economy, so I made the transition. I met with the leaders of the Division and remember feeling that a move to the captive regulatory division would become a place for me to learn and grow within such an interesting industry, while pursuing my professional development.
I recall being concerned about leaving public accounting because I enjoyed the variety of clients, but my skills transferred nicely, and what I quickly discovered is that the world of captive insurance is immense, dynamic, and ever-evolving, and the people I have met over the years are among some of the top reasons I’m passionate about the industry.
That was 27 years ago and it turned out to be the best decision I could have made for my career.
Who inspired you or acted as a mentor in your career?
Throughout my career, so many people have inspired me in their roles within their specific concentration of the industry.
I haven’t identified a formal mentorship structure throughout my regulatory career. I’ve certainly been supported in many ways, so believe mentorship can show up in ways we might not expect. I would categorise my predecessors as informal mentors of mine, especially as I climbed the regulatory career ladder within the Division.
I always admired how comfortable they were speaking in front of an audience, or among NAIC committees. I was encouraged early on to participate in speaking engagements, and they arranged my first speaking engagement to talk about captive insurance in a room full of traditional insurance examiners. Back then, captive insurance wasn’t as widely accepted. It had the effect of fuelling my passion for spreading good education about captive insurance.
My predecessors encouraged me to attend NAIC meetings and to get to know other regulators to expand my perspective and hopefully reciprocate. That was an interesting time, since many regulators were anti-captive. In working to break down barriers, I’ve made meaningful connections and expanded my understanding and respect for other people’s opinions.
Beyond the public meeting space, I was always encouraged to expand my knowledge by getting involved with projects outside of my day-to-day work activities. With some of that work, there have been many captive insurance professionals who were generous with their time and sharing their knowledge.
I find that people are eager to discuss their company, and their ideas, so it’s always a learning experience. When people come together there’s a lot to be gained from those discussions. It’s very supportive and collaborative.
What do you think deters people from entering the world of captives?
One historic limitation with hiring people into the industry is the perception of an insurance job as a salesperson. The world of captives has so much to offer. Some good initiatives exist to help spread more awareness about the industry as a career path, but more engagement and messaging about the interesting jobs people might not immediately think of (data analysis, safety and loss control, legal, and regulation, to name a few) would help to bring new talent into the mix.
How can mentorship and sponsorship programmes be designed to better support the career development of women?
Mentorship and sponsorship programmes are effective ways to support career development within the industry by connecting women with senior leaders who can advocate for them and provide guidance for advancement. There is an increasing number of programmes recognising and celebrating women in leadership roles within the industry, which promote visibility and inspiration to others.
Organisations and their leaders can be proactive in creating a more inclusive and supportive workplace culture. Proactive measures focused on training, professional development, networking and mentorships are great opportunities to learn about the industry’s diverse range of career paths, and to encourage support among employees by fostering a culture of feedback and transparency where employees feel comfortable sharing their experiences.
“Job-sharing, training, and rotating roles to bring women into the leadership fold can help build the necessary experience.”
In what ways can companies in the sector create a more inclusive culture that actively promotes gender diversity at all levels?
Companies can start by adopting policies for recruitment and advancement, communicate commitment to diversity and inclusion, and implement education involving that commitment. Additionally, companies should aim to support a quality work-life balance for all employees. An ongoing review and adjustment of salaries can help to ensure pay equity.
Offering equal access to training, mentorship, and advancement opportunities, plus implementing a transparent system for recognising achievements, are all significant ways for companies to create a healthy workplace culture everyone will benefit from.
What challenges are gender-specific to women in the captives industry?
The industry has been making great strides for gender equality in recent years, but women are still under-represented in a few ways.
I would estimate 50 percent of the workforce consists of women, but only 20 percent of leadership or executive level positions are occupied by women.
Gender bias still exists when it comes to career advancement. Historically, there have been limited opportunities and a lack of support for women looking to enter and for advancement in captive insurance careers, but I believe that is changing. Equal pay for equal work continues to be a challenge.
What solutions would you like to see?
I would like to see growth in initiatives for education, networking and mentoring. Organisations within the captives sector have a vested interest in creating equal opportunities because it fosters greater levels of creativity and innovation through a more diverse pool of perspectives and ideas.
Job-sharing, training, and rotating roles to bring women into the leadership fold can help build the necessary experience. Women possess valuable skills, that may go unseen or undemonstrated if they are stuck in the same roles within the industry.
Leaders within the industry can work to create opportunities for women to show initiative and build upon their strengths in the workplace.
What are your ambitions?
I’m motivated by the future and the talent that will extend beyond my time in the captive insurance industry. Because of that, I strive to set a standard and drive change that benefits everyone. In addition to adding value to my day-to-day work responsibilities, I’m passionate about sparking interest in others, fostering a supportive culture, and navigating a path forward that advances equality, innovation and growth.
Click here to read Captive International’s first Influential Women in Captive Insurance publication, celebrating the women transforming the captive sector through their sustained excellence and leadership.
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